Methanesulfonyl chloride → N-(4-Ethenyl-2-fluorophenyl)methanesulfonamide

Reaction equation

[F:1][C:2]1[CH:8]=[C:7]([CH:9]=[CH2:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:11][S:12](Cl)(=[O:14])=[O:13]>N1C=CC=CC=1.O>[F:1][C:2]1[CH:8]=[C:7]([CH:9]=[CH2:10])[CH:6]=[CH:5][C:3]=1[NH:4][S:12]([CH3:11])(=[O:14])=[O:13]

Participants

Procedure

A cooled solution of 2-Fluoro-4-vinylaniline (20-1, 0.96 g, 7 mmol) in pyridine (10 mL) at 0° C. was treated with methanesulfonyl chloride (0.644 mL, 8.4 mmol) and stirred at room temperature for 30 min. The reaction mixture was diluted with water and extracted with EtOAc several times. The combined organic layers were washed with water and brine, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:3) as eluant to afford N-(2-Fluoro-4-vinylphenyl)methanesulfonamide (20-2, LJO-325, 1.372 g, 91%) as a white solid.